Tech's Stubborn Perennials: The Problems We Should Have Solved by Now

How Essential Digital Infrastructure Remains Trapped in Amber While Generative AI Rewrites Our Future

Doctors still communicate life-critical information via fax machines. Meeting scheduling remains a multi-platform negotiation ritual. Online payment systems proliferate like digital kudzu, each incompatible with the other. And every April, Americans participate in a bizarre tax calculation ceremony that the government could easily perform automatically.

These aren't exotic edge cases. They're core functions of modern life, digital perennials that refuse to wither despite decades of supposed innovation. While venture capital chases the next shiny distraction, these fundamental problems remain trapped in amber—technological anachronisms preserved by some combination of misaligned incentives, regulatory capture, and collective inertia.

The persistence of these solvable problems becomes more striking when juxtaposed against our recent technological leaps. We've created AI systems sophisticated enough to generate convincing legal briefs, yet somehow can't standardize calendar invitations across platforms. The contrast would be comical if it weren't so consequential.

The Secure Communication Paradox

Healthcare professionals in America still rely on fax machines—technology predating the internet—as the primary means of transmitting patient information. This isn't because doctors harbor nostalgic affection for the screech of modems or the gentle flutter of thermal paper. It's because fax, remarkably, remains more HIPAA-compliant than email.

Think about that. In an era when AI assistants can draft personalized correspondence and summarize complex medical research, healthcare providers communicate via technology that peaked during the Reagan administration. The underlying problem isn't technological capability—it's a failure of standards, incentives, and implementation.

Email protocols were designed when digital trust was assumed rather than earned. The fundamental architecture prioritized openness over security, making robust encryption an afterthought rather than a foundation. Decades later, we're still paying for this original sin, patching a system that wasn't built for the threats it now faces.

Meanwhile, secure messaging apps proliferate in personal communication. Signal, WhatsApp, and others offer end-to-end encryption by default, making them theoretically more secure than most enterprise email systems. Yet these consumer tools remain largely disconnected from professional workflows due to compliance concerns, administrative overhead, and organizational inertia.

The painful irony: we know how to build secure communication systems. We simply haven't created the conditions necessary for their universal adoption in professional contexts.

Calendar Coordination: The Meeting About Meetings

"What times work for you next week?" begins the ritualistic dance. What follows might involve Outlook invites, Google Calendar sharing, Calendly links, or—for the truly dedicated—exhaustive email threads listing available time slots with timezone specifications.

Calendar coordination remains unnecessarily complex because we've built dozens of siloed scheduling systems rather than one universal standard. Each platform offers features the others lack while remaining fundamentally incompatible without third-party bridges. The iCalendar standard exists but suffers from inconsistent implementation across platforms, making it less reliable than it should be.

The time wasted on this coordination rivals the meetings themselves. Studies suggest professionals spend an average of 4.8 hours per week scheduling meetings—time that could be spent on the actual work the meetings are meant to address. Each clumsy platform transition introduces friction into workflows already strained by information overload.

The frustration compounds when considering that our phones track our location, our fitness trackers monitor our sleep cycles, and our AI assistants synthesize complex research—yet we still manually negotiate when to talk to each other. This isn't a technological limitation but an ecosystem failure.

Payment Fragmentation: The Digital Wallet Explosion

Online payment options have evolved from "we only accept checks" to a dizzying array of digital wallets, each with its own ecosystem and limitations. Does this merchant take Apple Pay? Google Pay? PayPal? Venmo? The mental overhead of maintaining multiple payment systems—each with different security models, user experiences, and fee structures—creates unnecessary cognitive load.

The core technology for secure, efficient digital payments exists. Cryptographic verification, near-field communication, and biometric authentication provide the necessary building blocks. Yet merchants and consumers face a fragmented landscape reminiscent of early electricity adoption, when different cities used incompatible electrical standards.

This fragmentation persists despite clear evidence that payment friction directly impacts conversion rates. Studies consistently show that each additional step in a checkout process increases abandonment rates. Yet the competitive dynamics of the payment processing industry incentivize creating walled gardens rather than interoperable systems.

The blockchain community promised to solve this through decentralized finance but instead created yet another layer of complexity and fragmentation. Rather than simplifying payments, cryptocurrency introduced new technical requirements, volatile exchange rates, and uncertain regulatory frameworks—all undermining the core promise of frictionless transactions.

Tax Filing: Regulatory Capture in Plain Sight

Perhaps no technological anachronism better illustrates the power of misaligned incentives than the American tax filing system. The IRS already knows most of the information needed to calculate tax obligations for the majority of Americans. In many countries, tax authorities send pre-filled forms for citizens to verify rather than requiring them to calculate their taxes from scratch.

This isn't primarily a technological problem—it's regulatory capture in its purest form. Tax preparation companies like Intuit have lobbied extensively to prevent the simplification of tax filing, protecting a market estimated at over $11 billion annually. The Free File Alliance, ostensibly created to provide free tax filing for eligible Americans, has consistently underperformed, with only a small percentage of eligible taxpayers using these services.

The result is a system where Americans collectively spend about 2 billion hours and $30 billion annually on tax compliance—time and money that could be directed toward more productive endeavors. The technology for automatic tax filing exists; what's missing is the political will to implement it against entrenched interests.

This example highlights how technological stagnation often reflects power structures rather than technical limitations. The persistence of inefficient systems frequently benefits someone, even as it imposes costs on everyone else.

Breaking the Pattern

These perennial problems share common characteristics. They persist in domains where:

1. Network effects create winner-take-all dynamics
2. Entrenched interests benefit from maintaining the status quo
3. Coordination problems prevent adoption of universal standards
4. Short-term incentives undermine long-term infrastructure investment

Solving these issues requires more than technical innovation—it demands realignment of incentives, regulatory intervention, and collective action. We need digital infrastructure that prioritizes interoperability, security, and user experience over walled gardens and rent extraction.

Open standards have succeeded in other domains. The web itself exists because HTTP and HTML provided common protocols for information exchange. Similarly, SMS succeeded not because it was technically superior but because it worked universally across carriers and devices. These examples demonstrate the power of well-implemented standards to overcome coordination problems.

Perhaps there's hope in the current wave of AI advancement. Systems that can understand natural language could potentially bridge incompatible platforms, creating interoperability layers above fragmented infrastructure. Scheduling assistants already demonstrate this capability on a limited scale, negotiating across calendar systems with increasing fluency.

Yet technology alone won't solve problems rooted in misaligned incentives. Addressing regulatory capture requires political will, while overcoming coordination problems demands industry cooperation against short-term competitive instincts.

For professionals navigating these inefficiencies daily, the best strategy often involves embracing flexibility rather than seeking perfect solutions. Use multiple payment systems. Maintain calendar redundancy. Accept that email security requires additional layers of protection. And yes, keep that fax machine operational—at least for now.

The technical capacity to solve these problems exists. The challenge lies in creating the conditions necessary for their implementation—aligning incentives, establishing standards, and building bridges across digital islands. Until then, these perennial problems will continue to bloom, reminders that progress isn't evenly distributed across our digital landscape.

The next time your AI assistant crafts a perfect email while you struggle to coordinate a simple meeting across platforms, remember: technology advances rapidly, but infrastructure evolution follows its own stubborn timeline. The distance between what's possible and what's implemented remains the most consistent feature of our digital age.